Synthesis of 1,2-dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes
Overview
Chemistry
Authors
Affiliations
[reaction: see text] The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.
Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides.
Yaremenko I, Radulov P, Belyakova Y, Fomenkov D, Tsogoeva S, Terentev A Pharmaceuticals (Basel). 2022; 15(4).
PMID: 35455469 PMC: 9025639. DOI: 10.3390/ph15040472.
Five-Membered Ring Peroxide Selectively Initiates Ferroptosis in Cancer Cells.
Abrams R, Carroll W, Woerpel K ACS Chem Biol. 2016; 11(5):1305-12.
PMID: 26797166 PMC: 5507670. DOI: 10.1021/acschembio.5b00900.
[3+2] Photooxygenation of aryl cylopropanes via visible light photocatalysis.
Lu Z, Parrish J, Yoon T Tetrahedron. 2014; 70(27-28):4270-4278.
PMID: 25170179 PMC: 4142714. DOI: 10.1016/j.tet.2014.02.045.
Terentev A, Borisov D, A Vil V, Dembitsky V Beilstein J Org Chem. 2014; 10:34-114.
PMID: 24454562 PMC: 3896255. DOI: 10.3762/bjoc.10.6.
Generation of singlet oxygen from fragmentation of monoactivated 1,1-dihydroperoxides.
Hang J, Ghorai P, Finkenstaedt-Quinn S, Findik I, Sliz E, Kuwata K J Org Chem. 2012; 77(3):1233-43.
PMID: 22283731 PMC: 3279295. DOI: 10.1021/jo202265j.